6-bromo-1-phenyl-1H-benzo[d]imidazole → 6-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-1-phenyl-1H-benzoimidazole

HRID 2202455Notes

Reaction equation

HRID 2202455 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:6]=2[CH:16]=1.[F:17][C:18]1[CH:23]=[CH:22][C:21]([N:24]2[C:28](B(O)O)=[CH:27][CH:26]=[N:25]2)=[CH:20][CH:19]=1>>[F:17][C:18]1[CH:19]=[CH:20][C:21]([N:24]2[C:28]([C:2]3[CH:3]=[CH:4][C:5]4[N:9]=[CH:8][N:7]([C:10]5[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=5)[C:6]=4[CH:16]=3)=[CH:27][CH:26]=[N:25]2)=[CH:22][CH:23]=1

Participants

3

Reactant 2

HCID 202668606-bromo-1-phenyl-1H-benzo[d]imidazole2×HCID 900951701-(4-Fluorophenyl)-1H-pyrazol-5-ylboronic acid2×

Product 1

HCID 736734286-[2-(4-Fluoro-phenyl)-2H-pyrazol-3-yl]-1-phenyl-1H-benzoimidazole

Procedure

The title compound, off-white solid (39 mg, 30%), MS (ISP) m/z=355.2 [(M+H)+], mp 201° C., was prepared in accordance with the general method of example 1 from 6-bromo-1-phenyl-1H-benzo[d]imidazole (intermediate E) (100 mg, 366 μmol) and 1-(4-fluoro-phenyl)-1H-pyrazol-5-ylboronic acid (intermediate A) (98.0 mg, 476 μmol).

Sources & evidence

ORD record
ord-945ee0b0b98f428fa84d5d53abdc6f81
Source dataset
uspto-grants-2016_06
Patent number
US09365550B2

Reaction notes

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